Benzaldehyde → 1,4-Pentadien-3-one, 1-(4-methoxyphenyl)-5-phenyl-, (E,E)-

HRID 77677

反応式

HRID 77677 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.[OH-].[Na+].O.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](=[O:13])[CH:12]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 954144-(4-Methoxyphenyl)but-3-en-2-one

生成物 1

HCID 7605101,4-Pentadien-3-one, 1-(4-methoxyphenyl)-5-phenyl-, (E,E)-収率 96.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

1-(4-Methoxyphenyl)-1-buten-3-one (35e, 0.29 g, 1.6 mmol) was dissolved in methanol (5 ml) and stirred for 5 min at room temperature. A solution of sodium hydroxide (0.14 g, 3.5 mmol) and water (5 ml) was added and the mixture stirred for 30 min at room temperature. Benzaldehyde (1b, 0.17 ml, 1.7 mmol) was added dropwise and the mixture stirred for 18 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethanol to give 0.41 g (94%) of a yellow solid: mp 85-89° C. [expected mp 118-119° C.]; 1H NMR: δ 3.82 (s, 3H), 6.91 (d, 2H, J=8.5 Hz), 6.94 (d, 1H, J=15.9 Hz), 7.06 (d, 1H, J=16.1 Hz), 7.38 (m, 4H), 7.57 (m, 3H), 7.71 (dd, 2H, J=15.9, 2.0 Hz); 13C NMR: δ 55.4, 114.4, 123.3, 125.5, 127.4, 128.2, 128.8, 130.0, 130.2, 134.8, 142.6, 143.0, 161.5, 188.6.

後処理

  1. stirringthe mixture stirred for 30 min at room temperature
  2. stirringthe mixture stirred for 18 hr at room temperature
  3. filtrationThe resulting precipitate was filtered
  4. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-5f6605a5b4044f2f810367de70af7ec3
出典データセット
uspto-grants-2014_09
特許番号
US08841326B2

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